Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 29, Pages 8989-8993Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201804128
Keywords
cellular uptake; fluorescent molecules; halogens; MCT8 transporter; thyroid hormones
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Funding
- Science and Engineering Research Board (SERB), Department of Science and Technology (DST), New Delhi [EMR/IISc-01/2016]
- Indian Institute of Science, Bangalore
- SERB
- SERB of J. C. Bose National fellowship [SB/S2/JCB-067/2015]
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Small-molecule-based fluorescent probes have become important tools in biology for sensing and imaging applications. However, the biological applications of many of the fluorescent molecules are hampered by low cellular uptake and high toxicity. In this paper, we show for the first time that the introduction of halogen atoms enhances the cellular uptake of fluorescent molecules and the nature of halogen atoms plays a crucial role in the plasma membrane transport in mammalian cells. The remarkably higher uptake of iodinated compounds compared to that of their chloro or bromo analogues suggests that the strong halogen bonding ability of iodine atoms may play an important role in the membrane transport. This study provides a novel strategy for the transport of fluorescent molecules across the plasma membrane in living cells.
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